I was thinking about this the other day. With regular wear, say, even once or twice a week, my Clarks give out after about 2-3 years. At 100 a shot, I'm wondering if it's worth buying these again. On the other hand, Red Wing Heritage has some great looking chukkas, and I know those would be a much longer-lasting shoe, maybe even a lifetime shoe. More expensive initial at over $200, but worth it.